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Über 4,4,6-trisubstituierte 3,4-Dihydro-2(1H)-pyrimidinimine, Hexahydro-2(1H)-chinazolinimine bzw.-one bzw.-thione und Spiro[cycloalkan-1,4′(1′H)-cycloalkeno-pyrimidin]-2′ (3′H)-imine

Preparation and properties of 4,4,6-trisubstituted 3,4-dihydro-2(1H)-pyrimidinimines, hexahydro-2(1H)-quinazolinimines resp.-ones resp.-thiones and spiro[cycloalkan-1,4′(1′H)-cycloalkenopyrimidin]-2′ (3′H)-imines

Über Heterocyclen, 44. Mitteilung

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Abstract

The 2-alken-1-ones2 b, 2 c and3–8, which have very different structures, were reacted with guanidine to give cyclic compounds:2 b and2 c resp. are transformed by guanidine to the trisubstituted 3,4-dihydro-2(1H)-pyrimidinimines1 b and1 c resp., action of guanidine on the cyclo-hexylidenaceton (3) yields 4-methyl-1,3-diaza-4-spiro[5,5]-undecen-2-imine (11); isopropylidencyclohexanone4 and the isomeric (methylcyclohexenyl)ethanone5 condense with guanidine resp. urea resp. NH4CNS to give 4,4-dimethyl-3,4,5,6,7,8-hexahydro-2(1H)-quinazolinimine (15), resp.-one (16), resp.-thione (17) and 4,8a-dimethyl-3,4,6,7,8,8a-hexahydro-2(1H)-quinazolinthione (19). With the cycloalkyliden-alkanones6–8 guanidine reacts to yield the spiro[cycloalkan-1,4′(1′H)-cycloalkenopyrimidin]-2′(3′H)-imines24–26. The structure of the compounds cited is derived from their NMR-and (partially) mass spectra; from most of the bases picrates were also synthesized.

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Correspondence to Winfried Wendelin.

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Herrn Prof. Dr.H. Grubitsch zum 70. Geburtstag gewidmet.

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Wendelin, W., Harler, A. & Fuchsgruber, A. Über 4,4,6-trisubstituierte 3,4-Dihydro-2(1H)-pyrimidinimine, Hexahydro-2(1H)-chinazolinimine bzw.-one bzw.-thione und Spiro[cycloalkan-1,4′(1′H)-cycloalkeno-pyrimidin]-2′ (3′H)-imine. Monatshefte für Chemie 107, 141–154 (1976). https://doi.org/10.1007/BF00909091

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